Dimethylformamide → 8-Methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazine

HRID 433066Notes

Reaction equation

HRID 433066 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]3[CH2:13][C:14]4C([C:11]3=[C:10](C=O)[C:9]=2[N:22]=1)=CC=C[CH:15]=4.CN(C)C=[O:26]>>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]3[C:11]([O:26][CH2:15][CH2:14][CH2:13]3)=[CH:10][C:9]=2[N:22]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 187582162-Methoxy-6H-pyrido[2',3':4,5]pyrrolo[2,1-a]isoindole-11-carbaldehyde

Product 1

HCID 114014538-Methoxy-3,4-dihydro-2H-pyrido[2',3':4,5]pyrrolo[2,1-b][1,3]oxazine

Conditions

Temperature
0 °C

Procedure

Under an inert atmosphere, 160 mg (4 mmol) of sodium hydride (60% in oil) are added slowly at 0° C., to a solution of 380 mg (1.34 mmol) of the compound obtained in Step E in 10 ml of N,N-dimethylformamide. The reaction mixture is stirred at 0° C., for 30 minutes before being hydrolysed with ice and then extracted with ethyl acetate. The organic phase is washed several times with water, dried over magnesium sulphate, concentrated and purified by flash chromatography over silica gel (eluant:ethyl acetate/petroleum ether, 95:5) to yield the title compound in the form of a brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed several times with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. custompurified by flash chromatography over silica gel (eluant:ethyl acetate/petroleum ether, 95:5)

Sources & evidence

ORD record
ord-211e575ba0fb4516b2c471e468cb0312
Source dataset
uspto-grants-2003_12
Patent number
US06667304B2

Reaction notes

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